Berkshires Vacation Rentals

107 Properties, sort by: 
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Lovely Lenox Colonial with mountain views yet one mile from center of town

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 174313
Lenox house rental - Front of house
4 Bedrooms, Sleeps 9
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, rural
  • washing machine
Rates per property (USD)
$250 - $450/night
$2,000 - $3,500/week
$6,500 - $11,000/month
View Property Details Contact the Owner

New private carriage house in the woods

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 184864
Becket house rental - front view of carriage house
1 Bedroom, Sleeps 5
  • House
  • 1 Bathroom
  • mountain, rural
  • accept credit card
Rates per property (USD)
$160 - $175/night
$825 - $950/week
View Property Details Contact the Owner

Nestled in a valley of mountains and close to Lenox, Tanglewood Skiing

  1. Massachusetts,
  2. Berkshires,
  3. Dalton Vacation Home Rentals
— Property 145825
Dalton house rental - Open floor plan main level
5 Bedrooms, Sleeps 12
  • House
  • 3 Bathrooms
  • lake, mountain
  • swimming pool
Rates per property (USD)
$350 - $550/night
$1,800/week
$4,500 - $7,000/month
View Property Details Contact the Owner

Rare Town Center Location in Lenox

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 114969
Lenox house rental - Front exterior with antique porch
3 Bedrooms, Sleeps 7
  • House
  • 2 Bathrooms, 1 Half Bath
  • town, village
  • air-conditioning
Rates per property (USD)
$1,800/week
$9,500/month
View Property Details Contact the Owner

Cozy 3BR/2bath - Escape the crowds & relax at home!

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 145582
Hancock house rental - Fully Furnished Seasonal Rental
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$350/night
View Property Details Contact the Owner

Beautiful New England Home, Walk to Tanglewood

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 114464
Lenox house rental
4 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom, 1 Half Bath
  • mountain, town
  • air-conditioning
View Property Details Contact the Owner

Mountainside Luxury Retreat in the Berkshires with Breathtaking Views!

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 173438
Lee house rental - Open kitchen, breakfast room with amazing views!
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, town
  • accept credit card
Rates per property (USD)
$2,000/week
$4,000 - $10,000/month
View Property Details Contact the Owner

Early 1800s Greek Revival Farmhouse

  1. Massachusetts,
  2. Berkshires,
  3. Stockbridge Vacation Home Rentals
— Property 124735
Stockbridge house rental - Front of house
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • town
  • air-conditioning
View Property Details Contact the Owner

Berkshires Vacation Home on Hayden Pond

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 187303
Otis house rental - Charming and Welcoming Farm House
6 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • lake, waterfront
  • washing machine
Rates per property (USD)
$800 - $1,000/week
View Property Details Contact the Owner

Ski the Berkshires from House on Lake Garfield Monterey

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Vacation Home Rentals
— Property 170562
Monterey house rental - Ski House
4 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • town, waterfront
  • internet access
Rates per property (USD)
$1,600/month
View Property Details Contact the Owner

Quaint Three Bedroom House in the Berkshire Mountains Five-minute Walk from Will

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 311008
Williamstown house rental
3 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom
  • mountain, village
  • washing machine
View Property Details Contact the Owner

Charming, Berkshires Ski/Lakehouse....country setting...only 6 miles to Gt Barr.

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 109882
Great Barrington house rental - Front of House
3 Bedrooms, Sleeps 5
  • House
  • 1 Bathroom, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$200 - $250/night
$1,400 - $2,000/week
$3,000 - $6,000/month
View Property Details Contact the Owner

Jem's Berkshire Rental

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 152703
Great Barrington house rental - House view
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, town
  • accept credit card
Rates per property (USD)
$500/night
$2,800/week
$9,000/month
View Property Details Contact the Owner

Beautiful Spacious Wooded Home with Access to Lake Offering Swimming and Boating

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 319198
Becket house rental
4 Bedrooms, Sleeps 12
  • House
  • 2 Bathrooms, 1 Half Bath
  • washing machine
  • stereo system
Rates per property (USD)
$175 - $200/night
$1,000 - $1,500/week
$4,000 - $5,500/month
View Property Details Contact the Owner

Berkshires, Lake Buel Waterfront Cottage, May through Oct, 2009

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 183642
Great Barrington house rental - Private Cove
2 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom, 1 Half Bath
  • lake, waterfront
  • internet access
View Property Details Contact the Owner

Rustic Home in Exclusive Lakeside Community

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 178168
Otis house rental
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • swimming pool
Rates per property (USD)
$300/night
$1,500 - $2,000/week
$4,000 - $5,000/month
View Property Details Contact the Owner

Charming Downtown Williamstown Cottage

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 169199
Williamstown house rental
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • downtown, village
  • air-conditioning
View Property Details Contact the Owner

New England Country Home, 'Frog Hollow'

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 101823
Great Barrington house rental
4 Bedrooms, Sleeps 9
  • House
  • 2 Bathrooms, 1 Half Bath
  • rural
  • air-conditioning
Rates per property (USD)
$250 - $300/night
$850 - $2,100/week
$5,500 - $8,000/month
View Property Details Contact the Owner

Quiet Lake house with beautiful water views

  1. Massachusetts,
  2. Berkshires,
  3. Hinsdale Vacation Home Rentals
— Property 190256
Hinsdale house rental - View of the lake from the back porch.
2 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • lake, waterfront
  • washing machine
Rates per property (USD)
$140/night
$800 - $1,200/week
View Property Details Contact the Owner

Beautiful Bungalow Beside Babbling Brooks

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 111135
Becket house rental - The House and Deck in the Winter
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • air-conditioning
View Property Details Contact the Owner

Beautiful New Lindal Cedar Home with Great Lake Views

  1. Massachusetts,
  2. Berkshires,
  3. Hinsdale Vacation Home Rentals
— Property 156700
Hinsdale house rental - Front of House
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake
  • accept credit card
Rates per property (USD)
$2,000/week
$7,000/month
View Property Details Contact the Owner

Bright Sunny Berkshire Home

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 186835
Great Barrington house rental - View From Master Bedroom Deck
2 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • rural
  • internet access
Rates per property (USD)
$2,000/week
View Property Details Contact the Owner

Charming Lakefront on Stockbridge Bowl for Fall foliage

  1. Massachusetts,
  2. Berkshires,
  3. Stockbridge Vacation Home Rentals
— Property 132791
Stockbridge house rental - Lake view from back deck
3 Bedrooms, Sleeps 8
  • House
  • lake, rural
  • washing machine
View Property Details Contact the Owner

Tree Peepers Getaway/New Construction/4bd3.5bth

  1. Massachusetts,
  2. Berkshires,
  3. West Stockbridge Vacation Home Rentals
— Property 179961
West Stockbridge house rental
4 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • mountain, village
  • air-conditioning
Rates per property (USD)
$2,000 - $2,500/week
$5,500 - $8,500/month
View Property Details Contact the Owner

Cute Berkshires Cottage

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 124984
Otis house rental
3 Bedrooms, Sleeps 7
  • House
  • 3 Bathrooms
  • mountain, rural
  • washing machine
Rates per property (USD)
$800/week
$2,350/month
View Property Details Contact the Owner

Gorgeous Views in Lee with Sauna, Hot Tub, Sun-Bed, and More!

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 186615
Lee house rental
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms, 1 Half Bath
  • air-conditioning
  • washing machine
Rates per property (USD)
$1,800 - $2,200/week
$2,500 - $9,000/month
View Property Details Contact the Owner

Comfortable 5 Bdrm House -Great Get-a-Way!

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 150566
Lee house rental - Living room with an amazing view
5 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$36 - $365/night
$2,600/week
$9,000/month
View Property Details Contact the Owner

Private Setting in Lenox

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 207123
Lenox house rental - Living Room
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • resort, village
  • air-conditioning
Rates per property (USD)
$1,400 - $2,000/week
$2,500 - $7,000/month
View Property Details Contact the Owner

Whitman Woods: Private Berkshire Vacation, 4 acres

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 138408
Hancock house rental - Whitman Woods & House - summer
4 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • mountain, rural
  • washing machine
View Property Details Contact the Owner

Charming Berkshires Lakefront House with Beautiful Views

  1. Massachusetts,
  2. Berkshires,
  3. Cheshire Vacation Home Rentals
— Property 122780
Cheshire house rental - View of house from edge of lake
3 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom
  • lake, mountain
  • air-conditioning
Rates per property (USD)
$175 - $200/night
$850 - $1,150/week
View Property Details Contact the Owner
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